Ortho/Ipso Alkylborylation of Aryl Iodides

This work describes a method for the difunctionalization of aryl iodides to generate polysubstituted arenes via Pd catalysis. The reaction hinges on the unique interplay between norbornene and the metal catalyst to impart a guided ortho C–H alkylation event followed by a programmatic ipso borylation...

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Bibliographic Details
Published in:Organic letters 2019-11, Vol.21 (22), p.9251-9255
Main Authors: Sui, Xianwei, Grigolo, Thiago A, O’Connor, Colin J, Smith, Joel M
Format: Article
Language:English
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Summary:This work describes a method for the difunctionalization of aryl iodides to generate polysubstituted arenes via Pd catalysis. The reaction hinges on the unique interplay between norbornene and the metal catalyst to impart a guided ortho C–H alkylation event followed by a programmatic ipso borylation to provide a diverse array of substituted arene products. The utility of this transformation is demonstrated through the functionalization of the boronic ester to a variety of valuable functionalities.
ISSN:1523-7060
1523-7052
DOI:10.1021/acs.orglett.9b03674